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Volume 56, Issue 9
Displaying 1-33 of 33 articles from this issue
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Review
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Transition Metal-Catalyzed Asymmetric Reactions Using P-Chirogenic Diaminophosphine Oxides: DIAPHOXsTetsuhiro NemotoArticle type: Review
2008 Volume 56 Issue 9 Pages 1213-1228
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThis review describes the development of a new class of chiral phosphorus ligands: amino acid-derived P-chirogenic diaminophosphine oxides, DIAPHOXs, and their application to several transition metal-catalyzed asymmetric allylic substitution reactions. Pd-catalyzed asymmetric allylic alkylation with cyclic β-keto esters as prochiral nucleophiles was initially examined using P-chirogenic diaminophosphine oxide 1a, resulting in highly enantioselective construction of quaternary stereocenters. Mechanistic investigations revealed that 1a is activated by N,O-bis(trimethylsilyl)acetamide-induced tautomerization to afford a trivalent diamidophosphite species 13, which functions as the actual ligand. Pd-catalyzed asymmetric allylic substitutions of both acyclic and cyclic substrates were also examined using various nucleophiles such as malonate derivatives, nitromethane, aliphatic amines, and aromatic amines, providing a variety of chiral compounds with good to excellent enantioselectivity. In addition, Ir-catalyzed asymmetric allylic amination and alkylation of terminal allylic carbonates were examined using structurally optimized P-chirogenic diaminophosphine oxides, and the corresponding branched products were obtained in a highly regio- and enantioselective manner. Furthermore, the developed catalytic asymmetric process was successfully applied to the catalytic enantioselective synthesis of biologically active compounds, (R)-preclamol, (R)-baclofen hydrochloride, and (−)-paroxetine.View full abstractDownload PDF (698K)
Regular Articles
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Zhiqiang Zhang, Gallant Kar-Lun Chan, Jieliang Li, Wang-Fun Fong, Hon- ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1229-1233
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThe intracellular level of glutathione (GSH) was significantly decreased after the addition of andrographolide (1) to cell cultures of HepG2. When the molecular interaction between andrographolide and GSH was investigated under a condition mimicking the in vivo environment, we observed that the level of GSH dropped in the presence of andrographolide. Stoichiometric analysis indicates that the reaction between these two reactants was 1 to 1 at pH 7 and followed second order kinetics. The activation energy of the overall reaction was 41.9±10 kJ·mol−1 according to the Arrhenius equation. Using a micro-liquid–liquid extraction method followed by micellar electrokinetic chromatographic separation, two major products were isolated and identified, and their chemical structures were determined as 14-deoxy-12-(glutathione-amino)-andrographolide (2) and 14-deoxy-12-(glutathione-S-yl)-andrographolide (3). Based on these structural findings, a hypothetical mechanism of reaction between glutathione and andrographolide was proposed. It is concluded that the α,β-unsaturated lactone moiety of andrographolide reacts with GSH through a Michael addition followed by dehydration of the adduct.View full abstractDownload PDF (166K) -
Pramod Kumar, Sanjay Singh, Brahmeshwar MishraArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1234-1242
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSColon targeted delivery systems of metronidazole (MTZ) based on osmotic technology were developed. The developed systems consisted of osmotic core (drug, osmotic agent and wicking agent), coated with semipermeable membrane (SPM) containing guar gum as pore former, coated core were then further coated with enteric coating to protect the system from acidic environment of stomach. The effect of various formulation variables namely the level of wicking agent (sodium lauryl sulphate), osmotic agent in the osmotic core, the level of pore former (guar gum) in SPM, and the thickness of SPM, were studied on physical parameters and drug release characteristics of developed formulations. MTZ release was inversely proportional to SPM thickness, but directly related to the level of pore former, wicking agent and osmotic agent. On the other hand burst strength of the exhausted shells was decreased with the increase in level of pore former in the membrane but increased with the increase in the thickness of SPM. The drug release from the developed formulations was independent of pH, and agitation intensity, but dependent on the osmotic pressure of the release media. The thickness of enteric coating could prevent formation of delivery pores before contact with simulated colonic fluid, but had no effect on drug release. Result of SEM studies showed the formation of in-situ delivery pores in the membrane from where the drug release occurred, and the number of pores formed were directly related to the initial level of pore former (guar gum) in SPM. The manufacturing procedure was found to be reproducible and formulations were found to be stable during 3 months of accelerated stability studies.View full abstractDownload PDF (1502K) -
Ryoichi Sonoda, Masashi Horibe, Takao Oshima, Tomohiro Iwasaki, Satoru ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1243-1247
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThe dissolution property of a poorly water-soluble drug, flurbiprofen (FP), was improved by a novel dry coating method using a planetary ball mill. Several mixtures composed of water-soluble additives (D-mannitol, lactose, and erythritol), light anhydrous silicic acid, and flurbiprofen were prepared. These mixtures and several starches were co-ground in a planetary ball mill, and the surface of the starches was dry coated with the mixtures. The size, appearance, yield, and drug dissolution property of the dry coated preparations were evaluated, and the optimal formulation which improved the dissolution property of poorly water-soluble flurbiprofen was determined. The dissolution rate of FP was increased by dry coating of the surface of starches with microparticulated FP. It was further increased by co-grinding of FP, starch, and a water-soluble additive, or dry coating of the starch surface with microparticulated FP and light anhydrous silicic acid, as a glidant. These co-ground and dry coated preparations could be recovered from the pot of the planetary ball mill readily without adhesion to the inside wall of the pot. These are considered to be novel, industrially applicable methods for improving the dissolution rate of poorly water-soluble drugs.View full abstractDownload PDF (3056K) -
Xin Wei, Jian-Shuang Jiang, Zi-Ming Feng, Pei-Cheng ZhangArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1248-1252
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSFour novel anthraquinone-benzisochromanquinone dimers, named floribundiquinones A, B, C, and D (1—4), along with six known anthraquinones, 10-(chrysophanol-7′-yl)-10-hydroxychrysophanol-9-anthrane (5), physcion (6), chrysophanol (7), 1,5,8-trihydroxy-3-methyl-anthraquinone (8), aloe-emodin (9), and xanthorin (10), were isolated from the roots of Berchemia floribunda. Their structures including the absolute axial stereochemistry were elucidated on the basis of spectroscopic methods. Floribundiquinones represent a novel carbon skeleton with an anthraquinone-benzisochromanquinone unit. Hepatoprotective activities were evaluated against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.View full abstractDownload PDF (148K) -
Amany Ibrahim, Sherief Ibrahim Khalifa, Ishrak Khafagi, Diaa Tohamy Yo ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1253-1258
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSUrsolic acid (1) and kaempferol (3) are two major constituents of the Mediterranean plant Nerium oleander L. Microbial metabolism of (1) with Aspergillus flavus (ATCC 9170) resulted in the formation of 3-oxo-ursolic acid derivative, ursonic acid (2). On the other hand, Cunninghamella blakesleeana (ATCC 8688A) was able to convert (3) into kaempferol 3-O-β-D-glucopyranoside (4) as well as the new natural product kaempferol 4′-sulfate (5). Incubation of kaempferol with Mucor ramannianus (ATCC 9628) led to the isolation of one metabolite identified as kaempferol 4′-O-α-L-rhamnopyranoside (6). Transformation of kaempferol to the new compound kaempferol 7-O-β-D-4-O-methylglucopyranoside (7) and herbacetin 8-O-β-D-glucopyranoside (8) was observed after fermentation with Beauveria bassiana (ATCC 13144). Cytotoxic as well as antioxidant activities of the isolated metabolites were determined.View full abstractDownload PDF (119K) -
Tomohisa Moriguchi, Hideaki Sakai, Hideo Suzuki, Kazuo ShinozukaArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1259-1263
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSNovel phosphorothioate-modified oligodeoxynucleotides (S-ODNs) containing a deoxyuridine derivative bearing a spermine moiety at the C-5 position were synthesized. The study of the thermal stability and the thermodynamic stability showed that the modified S-ODNs have been able to form the stable duplexes with the complementary DNA. It was also found that the duplex composed of the modified S-ODN and its complementary RNA strand is the substrate for Escherichia coli RNase H, and the cleavage of the RNA strand by the enzyme was almost similar as in the case of the unmodified one.View full abstractDownload PDF (101K) -
Ai Kurume, Yasuhiro Kamata, Masayuki Yamashita, Qilong Wang, Hisashi M ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1264-1269
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSEleven 3-substituted isocoumarins and a benzylidenephthalide were synthesized through thermal cyclization reaction of δ- and γ-ketoamides, respectively. Subsequent deprotection of the hydroxyl groups of the resulting isocoumarin and benzylidenephthalide compounds afforded thunberginols A, B, and F, respectively, which originated from the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The synthesized isocoumarins and thunberginols were evaluated for their anti-allergic activity, in which thunberginol B exhibited the highest inhibitory potency on the degranulation of RBL-2H3 cells induced by antigen. Structure–activity relationship studies were carried out to determine the necessary substituents on the 3-phenylisocoumarin skeleton for inhibitory activity.View full abstractDownload PDF (165K) -
Phan Van Kiem, Mai Dinh Tri, Le Vo Dinh Tuong, Nguyen Huu Tung, Nguyen ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1270-1275
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTwo new phenyl glycosides, mangliesides A and B (1, 2), a new ionol glycoside, manglieside C (3), two new lignan glycosides, mangliesides D and E (4, 5), were isolated from the leaves of Manglietia phuthoensis, along with two known lignans, 3-methoxymagnolol (6) and obovatol (7). Their structures were established by means of 1D and 2D NMR, electrospray ionization (ESI)-MS and HR-ESI-MS experiments. Among them, compounds 2 and 5 significantly (p<0.05) increased the growth and differentiation of osteoblastic MC3T3-E1 cells in vitro.View full abstractDownload PDF (162K) -
Ping-Jyun Sung, Chen-Hao Pai, Tsong-Long Hwang, Tung-Yung Fan, Jui-Hsi ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1276-1281
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSChemical investigations on the sea whip gorgonian coral Junceella juncea have led to the isolation of five new 8-hydroxybriarane diterpenoids, junceols D—H (1—5). The structures of briaranes 1—5 were determined on the basis of spectroscopic methods and the methylenecyclohexane rings were found to exist in boat form in these new diterpenoids. Junceols D (1) and F—H (3—5) exhibited cytotoxicity toward CCRF-CEM and DLD-1 tumor cells and junceols E—H (2—5) displayed weak inhibitory effects on superoxide anion generation by human neutrophils.View full abstractDownload PDF (122K) -
Dong-Li Li, Xiao-Ming Li, Tie-Gang Li, Hong-Yue Dang, Peter Proksch, B ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1282-1285
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSFour new (1—4) and seven known (5—11) benzaldehyde derivatives were characterized from the liquid fermentation cultures of Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus. The structures of these compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compound 1, which was named as eurotirumin, possesses a new carbon skeleton with a cyclopentabenzopyran ring system.View full abstractDownload PDF (109K) -
Meng-Yuan Jiang, Fei Wang, Xiao-Long Yang, Li-Zhen Fang, Ze-Jun Dong, ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1286-1288
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSFour new natural products possessing vibralactone skeleton, 1,5-secovibralactone (1), vibralactone B (2), vibralactone C (3) and acetylated vibralactone (4), together with known compound vibralactone (5), had been isolated from cultures of the basidiomycete Boreostereum vibrans. The structures of 1—4 were elucidated on the basis of spectroscopic methods. The absolute configuration of 1 was suggested to be S by computational methods.View full abstractDownload PDF (79K) -
Maryam Sayyafi, Ali Abolhasani Soorki, Ayoob BazgirArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1289-1291
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSSynthesis of novel 1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-triones using one-pot, three components reaction of 1,2-dihydropyridazine-3,6-dione, dimedone and aldehydes under solvent-free conditions has been reported. These products were evaluated in vitro for their antibacterial activities.View full abstractDownload PDF (81K) -
Alexandre Nesterov, Jifu Zhao, David Minter, Carmen Hertel, Wenwen Ma, ...Article type: Regular Article
2008 Volume 56 Issue 9 Pages 1292-1296
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA series of diarylpropane compounds was isolated by screening a plant extract library for inhibitors of mushroom tyrosinase. The most potent compound, 1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)propane (UP302: CAS# 869743-37-3), was found in the medicinal plant Dianella ensifolia. Synthetic and plant-derived versions of UP302 inhibited mushroom tyrosinase with similar potencies. UP302 inhibited mushroom tyrosinase with Ki=0.3 μM, in a competitive and reversible fashion. UP302 was 22 times more potent than Kojic acid in inhibiting murine tyrosinase, with IC50 values of 12 and 273 μM respectively. Experiments on mouse melanoma cells B16-F1 and on human primary melanocytes demonstrated that UP302 inhibits melanin formation with IC50 values of 15 and 8 μM respectively. Long-term treatment of cultured melanocytes with up to 62 μM of UP302 revealed no detectable cytotoxicity. In a reconstructed skin model (MelanoDermTM) topical application of 0.1% UP302 resulted in significant skin lightening and decrease of melanin production without effects on cell viability, melanocyte morphology or overall tissue histology. In conclusion, UP302 is a novel tyrosinase inhibitor that suppresses melanin production in both cultured melanocytes and reconstructed skin with high potency and without adverse side effects.View full abstractDownload PDF (1184K) -
Masayuki Yoshikawa, Sachiko Sugimoto, Seikou Nakamura, Hisashi MatsudaArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1297-1303
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTwo acylated oleanane-type triterpene oligoglycosides, chakasaponins V and VI, an aromatic glycoside, chakanoside I, and an acylated flavonol oligoglycoside, chakaflavonoside A, were isolated from the flower buds of Chinese tea plant [Camellia sinensis (L.) O. KUNTZE]. The chemical structures of those new glycosides were elucidated on the basis of chemical and physicochemical evidence.View full abstractDownload PDF (232K) -
Mitsuteru Numazawa, Sachiko Komatsu, Takako Tominaga, Kouwa YamashitaArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1304-1309
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSAromatase, which is responsible for the conversion of androgens to estrogens, is a potential therapeutic target for the selective lowering estrogen level in patients with estrogen-dependent breast cancer. We prepared and tested series of the pyridine- and other heterocyclic ring-containing derivatives of 2- and 4-aminoestrones, estrone, and estradiol, compounds 5, 10, 12 and 15. The isonicotinyl derivatives of 2- and 4-aminoestrone, compounds 5c and 10c, were fairly potent competitive inhibitors of aromatase (Ki, 2.1±0.14 and 1.53±0.08 μM for 5c and 10c, respectively) and other compounds did not show, to a significant extent, the aromatase inhibitory activity. This result suggests that the isonicotinyl-substituted derivatives 5c and 10c would be accessible to the active site of aromatase.View full abstractDownload PDF (140K) -
Mamoru Kaname, Shigeyuki Yoshifuji, Haruki SashidaArticle type: Regular Article
2008 Volume 56 Issue 9 Pages 1310-1313
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThe ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon–carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine.View full abstractDownload PDF (127K)
Notes
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Ah-Reum Han, Hye-Young Min, Joo-Won Nam, Na-Youn Lee, Adam Wiryawan, W ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1314-1316
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA new naphthoquinone, (−)-3-[2-(acetyloxy)propyl]-2-hydroxy-8-methoxy-1,4-naphthoquinone (1) was isolated from the bulb of Eleutherine americana MERR. et HEYNE (Iridaceae) together with two known compounds, eleutherinol (6) and 1,5-dihydroxy-3-methylanthraquinone (7) which were found in this species for the first time. The other known compounds, (−)-isoeleutherin (2), (+)-eleutherin (3), (−)-hongconin (4), and (+)-dihydroeleutherinol (5) which were reported previously from this species, were also isolated in the present study. Compounds 2—6 exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 lipopolysaccharide-activated mouse macrophage cells with IC50 values of 7.7, 11.4, 19.8, 21.7, and 34.4 μM, respectively, whereas the other two compounds, 1 and 7, were inactive. The structure of compound 1 was elucidated by spectroscopic data analysis including 1D and 2D NMR experiments.View full abstractDownload PDF (100K) -
Sabira Begum, Syeda Qamar Zehra, Bina Shaheen SiddiquiArticle type: Notes
2008 Volume 56 Issue 9 Pages 1317-1320
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTwo new pentacyclic triterpenoids, namely lantanoic acid (1) and camaranoic acid (2), and six known compounds such as lantic acid, camarinic acid, camangeloyl acid, camarinin, oleanonic acid, and ursonic acid were isolated from the aerial parts of Lantana camara LINN. Structures of the new constituents were elucidated by chemical transformation and spectral studies including 1D (1H- and 13C-NMR) and 2D (1H–1H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), 1H–1H total correlation spectroscopy (TOCSY), J-resolved, 1H-detected heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC)) NMR spectroscopy.View full abstractDownload PDF (120K) -
Marlise Diane Jiofack Dongfack, Hanh Trinh Van-Dufat, Marie-Christine ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1321-1323
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThe MeOH extract of the stem barks of Drypetes tessmanniana (Euphorbiaceae) afforded two new triterpene derivatives characterized as 3β-O-(E)-3,5-dihydroxycinnamoyl-11-oxo-olean-12-ene and 3β,6α-dihydroxylup-20(29)-ene together with seven known compounds. Their structures were established on the basis of spectral analysis.View full abstractDownload PDF (95K) -
Zineddine Belhouchet, Marc Sautour, Tomofumi Miyamoto, Marie-Aleth Lac ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1324-1327
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTwo new steroidal saponins (1, 2) were isolated from the roots of Smilax aspera subsp. mauritanica (POIR.) ARCANG. (Liliaceae), together with the known curillin G (3), asparagoside E (4), asparoside A (5), asparoside B (6) and the phenolic compound resveratrol (7). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 3 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (minimum inhibitory concentrations of 25, 25 and 50 μg/ml, respectively) whereas the other compounds were inactive.View full abstractDownload PDF (97K) -
Somayeh Ahadi, Hamid Reza Khavasi, Ayoob BazgirArticle type: Notes
2008 Volume 56 Issue 9 Pages 1328-1330
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA simple, clean and efficient method for the synthesis of spiro[indoline-3,9′-xanthene]trione derivatives and spiro[acenaphthene-1,9′-xanthene]-1′,2,8′(2′H,5′H)-trione by condensation reaction of dimedone and isatins or acenaphthene in aqueous media is reported.View full abstractDownload PDF (120K) -
Nahoko Uchiyama, Kazuhiro Saisho, Ruri Kikura-Hanajiri, Yuji Haishima, ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1331-1334
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA new type of phosphodiesterase-5 (PDE-5) inhibitor, thioquinapiperifil (1), was found in dietary supplements. LC-MS analysis indicated that the supplements contain two major compounds. One was identified as thiodenafil (synonym: thiosildenafil) by direct comparison with the authentic compound. The other showed a molecular weight of 448, and accurate mass measurement showed its elemental composition to be C24H28N6O1S1. Together, the mass and NMR spectrometric data revealed that the compound is an imidazoquinazoline derivative: 3-ethyl-1,3-dihydro-8-[[[2-[4-(hydroxymethyl)-1-piperidinyl]phenyl]methyl]amino]-2H-imidazo[4,5-g]quinazoline-2-thione. This compound had been synthesized as a PDE-5 inhibitor, formerly reported as KF31327 by Kyowa Hakko Kogyo Co., Ltd. Considering this compound's general properties, it has been renamed thioquinapiperifil with the agreement of Kyowa Hakko Kogyo Co., Ltd. The detection of imidazoquinazoline-type compounds in dietary supplements has not been reported. Quantitative analysis showed that the contents of 1 and thiodenafil in the products were about 13—15 mg/tablet (43—48 μg/mg) and about 0.4 mg/tablet (1 μg/mg), respectively.View full abstractDownload PDF (101K) -
Motoki Inoue, Kaname Hashizaki, Hiroyuki Taguchi, Yoshihiro SaitoArticle type: Notes
2008 Volume 56 Issue 9 Pages 1335-1337
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSThe preparation and formation mechanism of n-hexadecane/water emulsions using natural β-cyclodextrin (β-CD) and chemically modified β-CDs (triacylated β-cyclodextrins) as an emulsifier were investigated. The stable water/oil (W/O) emulsion was formed using tripropanoyl-β-CD (TP-β-CD). From observation using the contact angle (θow) of precipitates derived from CD, it was clarified that oil/water (O/W) emulsion at θow<90° and (W/O) emulsion at θow>90° are formed when the composition of each oil and water was mixed with natural β-CD or triacylated β-CDs.View full abstractDownload PDF (2731K) -
Hui-Ying Han, Ping Wen, Hong-Wei Liu, Nai-Li Wang, Xin-Sheng YaoArticle type: Notes
2008 Volume 56 Issue 9 Pages 1338-1341
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSCampylotropis hirtella (FRANCH.) SCHINDL. was used as a folk medicine for the treatment of benign prostate hyperplasia (BPH) in China. In this study, two new coumarins, 7,2′,4′-trihydroxy-5-methoxy-3-arylcoumarin (1), 6-[(1S,2S*)-2-angeloyloxy-1,3-dihydroxy-3-methylbutyl]-7-methoxycoumarin, named angelol M (2), together with eleven known related compounds (3—13) were isolated from this plant under the bioassay guided fractionation. All the compounds showed activity with different levels in inhibiting prostate specific antigen (PSA) secreted from androgen dependent prostate cancer cell line, LNCaP cells, using ELISA method.View full abstractDownload PDF (112K) -
Lakshmi Narayana Bheemanapalli, Raghuram Rao Akkinepally, Shanthan Rao ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1342-1348
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA new series of 2,3,5,7-substituted-pyrido[2,3-d]pyrimidin-4(3H)-one derivatives were prepared from 2-amino-N,6-substituted phenyl-4-(trifluoromethyl or methyl)nicotinamides. The key intermediate 2-amino-N,6-substituted phenyl-4-(trifluoromethyl or methyl)nicotinamides were synthesized from 2-bromo-N,6-disubstituted phenyl-4-(trifluoromethyl or methyl)nicotinamides as well as from ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) coupling of 2-amino-4,6-substituted nicotinic acid and substituted arylamines. All the synthesized compounds were screened for antibacterial activity against Gram +ve and Gram −ve bacteria. Compound 7c showed better antibacterial activity against Gram +ve and Gram −ve bacteria.View full abstractDownload PDF (171K) -
Hirotaka Ishii, Yoshihito Okada, Masaki Baba, Toru OkuyamaArticle type: Notes
2008 Volume 56 Issue 9 Pages 1349-1351
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA new simple coumarin glycoside, named praeroside VI (1), along with six known coumarins, were isolated from an aqueous extract of Bai-Hua Qianhu, the root of Peucedanum praeruptorum DUNN. (Umbelliferae). Spectroscopic analysis and chemical studies were carried out to investigate the structure of the new coumarin, which was concluded to be 1. Additionally, two simple glycosidic coumarins and four simple nonglycosidic coumarins were identified as apiosylskimmin (2), hymexelsin (3), umbelliferone (4), scopoletin (5), isofraxidin (6) and 8-carboxy-7-hydroxy coumarin (7), respectively. This is the first reported identification of compound 7 as a constituent of plant materials.View full abstractDownload PDF (72K) -
Hui Yuan Gao, Li Jun Wu, Takahisa Nakane, Osamu Shirota, Masanori Kuro ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1352-1354
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTo isolate more rearranged lanostane-type triterpenes from Abies sachalinensis, continuous chemical investigation of the ethyl acetate soluble fraction of the methanol extract of A. sachalinensis afforded two new rearranged lanostane-type triterpenes (1, 2). Their structures were elucidated to be 3,4-seco-4(28),7,12,24-mariesatetraen-26,23-olide-23-hydroxy-3-oic acid (1) and ethyl 3,4-seco-8(14→13R)abeo-17,13-friedo-4(28),7,14,24-lanostatetraen-26,23-olide-23-hydroxy-3-oate (2), respectively. The structure of these compounds was determined by spectral studies, especially by two-dimensional (2D)-NMR and high-resolution (HR)-MS. Compounds 1 and 2 have a tautomeric lactone structure in the side chain.View full abstractDownload PDF (104K) -
Xiudong Yang, Trung Thang Khong, Li Chen, Hong Dae Choi, Jung Sook Kan ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1355-1356
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSTwo new 14-membered resorcyclic acid lactone derivatives, 8′-hydroxyzearalanone (1) and 2′-hydroxyzearalanol (2), and four known zearalanone derivatives (3—6) were isolated from the marine-derived fungus Penicillium sp. The structures of compounds 1—6 were elucidated by spectroscopic methods.View full abstractDownload PDF (83K) -
Yoko Araya, Jun-ichi Kasuga, Kenji Toyota, Yuko Hirakawa, Takuji Oyama ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1357-1359
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSBased on the result of X-ray crystallographic analysis of our peroxisome proliferator-activated receptor alpha and delta (PPARα/δ) co-agonist complexed with human PPAR ligand binding domain (LBD), we designed and synthesized an optically active fluorescent PPARα/δ co-agonist, which has a pyrene unit incorporated directly at the hydrophobic tail part of the structure as a fluorophore. This fluorescent co-agonist was applied in a homogeneous fluorescent polarization assay format for the identification of PPARδ ligands.View full abstractDownload PDF (571K) -
Na-Youn Lee, Hye-Young Min, Jun Lee, Joo-Won Nam, Yoo-Jin Lee, Ah-Reum ...Article type: Notes
2008 Volume 56 Issue 9 Pages 1360-1361
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSA new biflavanone, 2,2″,3,3″-tetrahydrorobustaflavone 7,4′,7″-trimethyl ether (1) was isolated from the whole plant of Selaginella doederleinii HIERON. (Selaginellaceae) together with the known biflavonoid, robustaflavone 7,4′,7″-trimethyl ether (2) as the cytotoxic constituents against the three human cancer cell lines, HCT, NCI-H358, and K562. The structure of the new compound 1 was elucidated by spectral analysis including various 1D- and 2D-NMR experiments.View full abstractDownload PDF (84K) -
Makoto Yoshida, Kentaro YamaguchiArticle type: Notes
2008 Volume 56 Issue 9 Pages 1362-1363
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSBromotyrosine alkaloids dispyrin (1), purpurealidin E (2), and aplysamine-1 (3) isolated from marine sponge, were synthesized from commercially available tyramine (4) as a common starting material. The overall yield was 18%, 39%, and 22% for 1 from 4 in 5 steps, 2 in 5 steps, and 3 in 6 steps, respectively.View full abstractDownload PDF (86K)
Communicatins to the Editor
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Youji Kitamura, Katsuya Mori, Makiko Yamamoto, Akira Nozaki, Madoka Sa ...Article type: Communications to the Editor
2008 Volume 56 Issue 9 Pages 1364-1366
Published: September 01, 2008
Released on J-STAGE: September 01, 2008
JOURNAL FREE ACCESSIn order to explore the capability of metal porphyrins as an alternative of horseradish peroxidase (HRP), HRP-like activi-ty of three manganese-porphyrins (Mn-Ps) and three Mn-octabromo-porphyrins (Mn-OBPs) was examined in both aqueous and immobilized states. It was found that Mn3+-octabromotetrakis(1-methyl-pyridinium-4yl)porphine (Mn-OBTMPyP) has an activity of at least 90% of HRP in an aqueous solution. Mn-OBTMPyP exhibited a catalytic activity even in the presence of hydrogen peroxide without suicide reaction. In addition, Mn-OBTMPyP was revealed to function as an alternative to HRP in the quantitative determination of serum uric acid. These results are of great interest because they indicate that metal-octabromo-porphyrins possibly include promising candidates of artificial enzyme capable of substituting for HRP.View full abstractDownload PDF (145K)
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